Patent GB-1308951-A (GB)
Title: Stabilization of phosphoric acid pesticides
IPC: C07F9/113
Filed: 1970-03-11
Abstract: 1308951 Stabilizing phosphoric acid pesticides CIBA-GEIGY AG 11 March 1970 [19 March 1969 12 March 1969 (2)] 11726/70 Heading ASE A pesticidal composition comprises (A) at least one pesticidal ester of phosphoric acid containing at least one alkyl group containing 1-3 carbon atoms; (B) as stabilizing agent, 0.1-10% by weight, based on the weight of (A), of at least one (i) compound of formula: or tautomer thereof of formula: or compound of formula wherein R represents a radical of hydroaromatic or of aromatic character comprising one, two or three rings, each having 5 or 6 ring members and when said radical contains two or three rings, the rings are condensed together or bound to each other, directly or via an oxygen atom or an -NH-, -CH 2 , or -CH=CH- group; the radical R being selected from (a) carbocyclic radicals of aromatic character having 1-3 rings and heterocyclic radicals of aromatic character having from 1-3 rings one of which rings contains one or two ring hetero atoms chosen from nitrogen, oxygen and sulphur; (b) carbocyclic character having two or three carbocyclic or heterocyclic radicals with hydroaromatic rings each of 5 or 6 ring members and at least two of these rings are condensed together, wherein two or four carbon atoms in one of the rings are saturated and at least one other ring is aromatic; (c) radicals as defined under (a) or (b) substituted by one or two phenylazo, napthylazo and/or arylazoarylazo (in which each of the aryl radicals is phenyl or naphthyl) groups; and (d) a radical as defined under (a), (b) or (c) with at least one of its rings bearing one to four substituents selected from fluorine, chlorine, bromine, iodine, keto oxygen, hydroxy, carboxy, alkyl having from one to six carbon atoms, alkenyl having from two to five carbon atoms, cycloalkyl having five or six carbon atoms, amino, alkanoylamino having up to five carbon atoms, mono-benzylamino, alkoxy having from one to five carbon atoms, benzyloxy, nitro, sulpho, cyano, amino substituted by one or two groups selected from alkyl groups having one to four carbon atoms, phenyl groups and benzyl groups, alkoxycarbonyl having from two to six carbon atoms, alkylsulphonyl having from one to five carbon atoms, sulphamoyl the nitrogen atom of which is unsubstituted or substituted by one or two hydrocarbon radicals having a total of one to eight carbon atoms, alkanoyloxy having at most eighteen carbon atoms, and alkenoyloxy having at most eighteen carbon atoms, alkanoyl having up to five carbon atoms and dialkylamino-alkyl having a total of from three to nine carbon atoms; and of 5 or 6 ring members and at least two of these rings are condensed together, wherein two or four carbon atoms in one of the rings are saturated and at least one other ring is aromatic; (c) radicals as defined under (a) or (b) substituted by one or two phenylazo, naphthylazo and/or arylazoarylazo (in which each of the aryl radicals is phenyl or naphthyl) groups; and (d) a radical as defined under (a), (b) or (c) with at least one of its rings bearing one to four substituents selected from fluorine, chlorine, bromine, iodine, keto oxygen, hydroxy, carboxy, alkyl having from one to six carbon atoms, alkenyl having from two to five carbon atoms, cycloalkyl having five or six carbon atoms, amino, alkanoylamino having up to five carbon atoms, mono-benzoylamino, alkoxy having from one to five carbon atoms, benzyloxy, nitro, sulpho, cyano, amino substituted by one or two groups selected from alkyl groups having one to four carbon atoms, phenyl groups and benzyl groups, alkoxycarbonyl having from two to six carbon atoms, alkylsulphonyl having from one to five carbon atoms, sulphamoyl the nitrogen atom of which is unsubstituted or substituted by one or two hydrocarbon radicals having a total of one to eight carbon atoms, alkanoyloxy having at most eighteen carbon atoms, and alkenoyloxy having at most eighteen carbon atoms, alkanoyl having up to five carbon atoms and dialkylamino-alkyl having a total of from three to nine carbon atoms; and R<SP>1</SP> is benzyl, alkyl of from H7 carbon atoms, alkenyl of two to eight carbon atoms or a radical R is defined under any one of (a) to (d) as defined above and R" is a radical R' as defined above, an unsubstituted phenylazo or naphthylazo group or a phenylazo or naphthylazo group substituted by methyl or ethyl; or R' and R" taken together represent a divalent hydrocarbon radical having a total of four to fourteen carbon atoms which is a straight or branched chain radical or a chain radical containing an aryl ring condensed to the chain, any substituent of said hydrocarbon radical being selected from the substituents defined under (d), and groups of the formula = NX (in which X represents hydrogen, alkyl having from one to five carbon atoms or phenyl), and the group of formula: represents a radical R as defined under (a) to (d) above other than a group at defined above wherein R' and R" are taken together, or (ii) salt of a compound as defined under (i) above bearing at least one group capable of salt formation, or (iii) metal complex of a compound or salt as defined under (i) or (ii) bearing one or two groups capable of metal complex formation selected from hydroxy, carboxy, amino, mono (C 1 -C 4 ) alkyl amino, phenylamino, phenylsulphonamido and (C 1 -C 4  alkyl) sulphonamido groups and, optionally (C) a solid or liquid solvent which is a solvent for component (A) and/or (B), component (B) being soluble in component (A) and/or (if present) component (C). The compositions may also contain other additives and active ingredients and many suitable compounds are specified, including essential oils, chlorbenzilate and chlorpropylate.